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Benzo[ c ]thiophene–C 60 Diadduct: An Electron Acceptor for p–n Junction Organic Solar Cells Harvesting Visible to Near‐IR Light
Author(s) -
Zhen Yonggang,
Obata Naoki,
Matsuo Yutaka,
Nakamura Eiichi
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200698
Subject(s) - thiophene , homo/lumo , fullerene , materials science , photochemistry , phthalocyanine , energy conversion efficiency , electron acceptor , organic solar cell , acceptor , electron donor , cycloaddition , optoelectronics , chemistry , nanotechnology , organic chemistry , molecule , catalysis , polymer , physics , condensed matter physics , composite material
We synthesized a new 56‐π‐electron fullerene derivative through a Diels–Alder cycloaddition of benzo[ c ]thiophene that featured a relatively low temperature, closer to stoichiometric use of the diene, and easy product purification. The 56‐π‐electron benzo[ c ]thiophene diadduct ( BTCDA ) has a LUMO energy level of 0.09 to 0.18 eV higher than that of 58‐π‐electron fullerenes, and therefore, the BTCDA ‐based organic photovoltaic device exhibited a higher open‐circuit voltage and power‐conversion efficiency (PCE). When used with a binary‐donor system, including visible‐light‐harvesting tetrabenzoporphyrin ( BP ) and near‐IR‐harvesting titanyl phthalocyanine ( TiOPc ), the device had a PCE that was 1.5–3 times higher (2.8 %) than that for devices with BP or TiOPc alone because the binary‐donor device can utilize light between λ =350 and 950 nm.